Cobalt(III)-mediated peptide synthesis. 1. Cobalt(III)-activated amino acid methyl esters and the synthesis of dipeptides

1981 ◽  
Vol 103 (23) ◽  
pp. 7023-7025 ◽  
Author(s):  
C. R. Clark ◽  
R. F. Tasker ◽  
D. A. Buckingham ◽  
D. R. Knighton ◽  
D. R. K. Harding ◽  
...  
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Amino Acid Methyl Esters

ChemInform Abstract: Cobalt(III)-Mediated Peptide Synthesis. Part 1. Cobalt(III)-Activated Amino Acid Methyl Esters and the Synthesis of Dipeptides.

1982 ◽  
Vol 13 (9) ◽  
Author(s):  
C. R. CLARK ◽  
R. F. TASKER ◽  
D. A. BUCKINGHAM ◽  
D. R. KNIGHTON ◽  
D. R. K. HARDING ◽  
...  
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Amino Acid Methyl Esters

2-Alkoxy-5(4H)-oxazolones from N-alkoxycarbonylamino acids and their implication in carbodiimide-mediated reactions in peptide synthesis

1981 ◽  
Vol 59 (2) ◽  
pp. 384-389 ◽  
Author(s):  
N. Leo Benoiton ◽  
Francis M. F. Chen
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Tertiary Amine ◽  
Acid Ester ◽  
Methyl Esters ◽  
Amino Acid Ester ◽  
Acid Methyl ◽  
Optically Pure ◽  
Amino Acid Methyl Esters

Reaction of N-ethyl,N′-(γ-dimethylaminopropyl)-carbodiimide- HCl with one equiv. of N-tert-butoxycarbonyl-L-valine (3a) in dichloromethane at 23 °C gives, besides the symmetrical anhydride (5a), the optically pure 2-tert-butoxy-4-isopropyl-5(4H)-oxazolone (4a) which can be obtained in 50% yield under selected conditions. The 2-benzyloxycarbonyl-4-isopropyl-5(4H)-oxazolone (4b) is similarly obtainable from N-benzyloxycarbonyl-L-valine (3b). Anhydrous acid converts 4a to the oxazolidinedione. Simple preparations of the N-carboxyanhydrides of valine and isoleucine have been devised from these reactions. Compound 4 reacts with 3 to give 5. Compound 4 reacts with an amino acid ester to give the optically pure peptide even in the presence of salts, but partial racemization occurs for reactions in the presence of a tertiary amine. Evidence for the implication of 2-alkoxy-5(4H)-oxazolones in the couplings of N-alkoxycarbonylamino acids is presented. Compound 4a has been isolated in 6–11% yield from carbodiimide-mediated reactions of 3a with itself or amino acid methyl esters which have been terminated before completion.

Highly Stereoselective Synthesis of Optically Pure C-Aryl Imines from α-L-Amino Acid Methyl Esters.

ChemInform ◽  
2004 ◽  
Vol 35 (17) ◽  
Author(s):  
Antonella Leggio ◽  
Adolfo Le Pera ◽  
Angelo Liguori ◽  
Anna Napoli ◽  
Claudio Romeo ◽  
...  
Keyword(s):  
Amino Acid ◽  
Stereoselective Synthesis ◽  
Methyl Esters ◽  
Acid Methyl ◽  
Optically Pure ◽  
Amino Acid Methyl Esters

ANTIMICROBIAL STUDIES OF NEWLY SYNTHESIZED 1H-BENZOTRIAZOLE-1-ACETYL-AMINO ACID METHYL ESTERS /PEPTIDE DERIVATIVES

INDIAN DRUGS ◽  
2013 ◽  
Vol 50 (12) ◽  
pp. 27-33
Author(s):  
K. Kaur ◽  
◽  
R Kaur ◽  
A. Kaur
Keyword(s):  
Amino Acid ◽  
1H Nmr Spectroscopy ◽  
Methyl Esters ◽  
Penicillium Expansum ◽  
Antimicrobial Compounds ◽  
Bacterial Strains ◽  
Antimicrobial Studies ◽  
Acid Methyl ◽  
Peptide Derivatives ◽  
Amino Acid Methyl Esters

Benzotriazole-1-acetic acid was coupled with amino acid methyl esters/ dipeptides/ tripeptides/tetrapeptides in the presence of DCC as a coupling agent and NMM as a base under continuous stirringfor 36 hrs. The reactions were monitored by TLC. The newly synthesized compounds were analyzedand the structures were confirmed by IR and 1H NMR spectroscopy. The synthesized compounds weretested against bacterial strains Bacillus subtilis, Staphylococcus aureus and Escherichia coli by usingciprofloxacin as standard in the concentration of 20?g/mL. All the compounds were also tested againstfungal strains Candida albicans, Aspergillus niger and Penicillium expansum by using fluconazole asstandard in the concentration of 10?g/mL. Compounds 1, 2, 3 and 4 were found to be more potent antimicrobial compounds.

Multifunctional lubricant additives derived from natural amino acids and methyl oleate

RSC Advances ◽  
2015 ◽  
Vol 5 (95) ◽  
pp. 77538-77544 ◽  
Author(s):  
Arukali Sammaiah ◽  
Korlipara V. Padmaja ◽  
Shiva Shanker Kaki ◽  
Rachapudi B. N. Prasad
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Oleate ◽  
Thioglycolic Acid ◽  
Methyl Esters ◽  
Lubricant Additives ◽  
Acid Methyl ◽  
Multifunctional Additives ◽  
Natural Amino Acids ◽  
Amino Acid Methyl Esters

Novel multifunctional additives were synthesized from methyl oleate via thioglycolic acid addition followed by condensation with different amino acid methyl esters.

One-pot synthesis of 4-arylidene imidazolin-5-ones by reaction of amino acid esters with isocyanates and α-bromoketones

2019 ◽  
Vol 17 (11) ◽  
pp. 3040-3047
Author(s):  
Jia-Yun Haung ◽  
Indrajeet J. Barve ◽  
Chung-Ming Sun
Keyword(s):  
Amino Acid ◽  
Multicomponent Reaction ◽  
Methyl Esters ◽  
Amino Acid Esters ◽  
One Pot ◽  
One Pot Synthesis ◽  
Acid Methyl ◽  
Acid Esters ◽  
Amino Acid Methyl Esters

A one-pot multicomponent reaction for assembling substituted 4-arylidene imidazolin-5-ones from l-amino acid methyl esters, iso-, isothio- or isoselenocyanates, and α-bromoketones has been discovered.

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